Dimethyl L-tartrate → HCID 19068731, compound

HRID 1957262

Reaction equation

HRID 1957262 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19](OC)OC)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:24]([C@@H:28]([C@H:30]([C:32]([O:34][CH3:35])=[O:33])[OH:31])[OH:29])([O:26][CH3:27])=[O:25]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19]3[O:31][CH:30]([C:32]([O:34][CH3:35])=[O:33])[CH:28]([C:24]([O:26][CH3:27])=[O:25])[O:29]3)[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 11851Dimethyl L-tartrateHCID 190687453-Chloro-2-(4-chloro-3-dimethoxymethylphenyl)-5-trifluoromethylpyridine

Product 1

HCID 19068731HCID 19068731, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

3.0 g of 3-chloro-2-(4-chloro-3-dimethoxymethylphenyl)-5-trifluoromethyl-pyridine, 5.4 g of dimethyl L(+)-tartrate and 100 mg of p-toluenesulfonic acid in 180 ml of anhydrous toluene were refluxed for 10 hours. The solution was cooled and then washed with 50 ml of 10% by weight sodium bicarbonate solution and three times with 50 ml of water each time, dried over sodium sulfate and concentrated. Chromatography on silica gel resulted in 3.0 g (77%) of colorless crystals; melting point: 48°-53° C.

Workup

  1. temperatureThe solution was cooled
  2. washwashed with 50 ml of 10% by weight sodium bicarbonate solution and three times with 50 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb05fe3833aa4722814b4a3f39fe5804
Source dataset
uspto-grants-1998_07
Patent number
US05783522

Linked notes

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